Prelog-Djerassi lactone

Base Information

• Chemical Name: Prelog-Djerassi lactone
• CAS No.: 69056-12-8
• Molecular Formula: C10H16O4
• Molecular Weight: 0
• UNII: A3VM4B9LHK
• Mol file: 69056-12-8.mol

Synonyms:Prelog-Djerassi lactone;A3VM4B9LHK;Prelog-djerassi lactone [MI];(+)-Prelog-Djerassi lactonic acid;UNII-A3VM4B9LHK;Prelog-djerassi lactonic acid, (+)-;69056-12-8;(alphaR,2S,3S,5R)-Tetrahydro-alpha,3,5-trimethyl-6-oxo-2H-pyran-2-acetic acid;H-Pyran-2-acetic acid, tetrahydro-alpha,3,5-trimethyl-6-oxo-, (alphaR,2S,3S,5R)-;(.ALPHA.R,2S,3S,5R)-TETRAHYDRO-.ALPHA.,3,5-TRIMETHYL-6-OXO-2H-PYRAN-2-ACETIC ACID;H-PYRAN-2-ACETIC ACID, TETRAHYDRO-.ALPHA.,3,5-TRIMETHYL-6-OXO-, (.ALPHA.R,2S,3S,5R)-

Chemical Property of Prelog-Djerassi lactone

Chemical Property:

• Vapor Pressure: 7.81E-07mmHg at 25°C
• Melting Point: 124-125°
• Boiling Point: 380.2°C at 760 mmHg
• Flash Point: 150.2°C
• Density: 1.107g/cm³
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 200.10485899
• Heavy Atom Count: 14
• Complexity: 249

Purity/Quality:

99% ^*data from raw suppliers

PRELOG-DJERASSI LACTONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CC(C(=O)OC1C(C)C(=O)O)C
• Isomeric SMILES: C[C@H]1C[C@H](C(=O)O[C@@H]1[C@@H](C)C(=O)O)C

Technology Process of Prelog-Djerassi lactone

There total 148 articles about Prelog-Djerassi lactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

(R)-2-((2S,3S,5R,6S)-6-Hydroxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-propionic acid (81310-01-2) → (+)-Prelog-Djerassi lactonic acid (69056-12-8)

Guidance literature:

With bromine; sodium acetate; In water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)82936-1

Reference yield: 94.0%

(3R,5S,6S)-6-[(R)-2-(10,10-Dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-1-methyl-2-oxo-ethyl]-3,5-dimethyl-tetrahydro-pyran-2-one → (+)-Prelog-Djerassi lactonic acid (69056-12-8)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 0.833333h;

DOI:10.1016/S0040-4039(96)02408-2

Reference yield: 94.0%

methyl <2S-<2α(S*),3β,5β>>-tetrahydro-α,3,5-trimethyl-6-oxo-2H-pyran-2-acetate (72367-05-6) → (+)-Prelog-Djerassi lactonic acid (69056-12-8)

Guidance literature:

With lithium hydroxide; In methanol; for 1h;

DOI:10.1021/jo00316a001

upstream raw materials:

lead(IV) tetraacetate

acetic acid

narbomycin

picromycin

Downstream raw materials:

(3R,5S,6S)-6-[(1S,2S,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-5-cyclohexyl-2-hydroxy-1,3-dimethyl-4-oxo-pentyl]-3,5-dimethyl-tetrahydro-pyran-2-one

(S)-2-((2R,3R,5R)-3,5-Dimethyl-6-oxo-tetrahydro-pyran-2-yl)-propionic acid

(R)-2-((2R,3R,5R)-3,5-Dimethyl-6-oxo-tetrahydro-pyran-2-yl)-propionic acid